In this paper, I focus on the debate that surrounds “pragmatic” interpretations of Ludwig Wittgenstein. By this, I mean the debate between those who read Wittgenstein as a pragmatist or as having pragmatic affinities and those who object to this reading. In particular, drawing on Hilary Putnam’s lecture “Was Wittgenstein a Pragmatist?” and Stanley Cavell’s response “What’s the Use of Calling Emerson a Pragmatist?,” I will spell out the similarities seen between Wittgenstein and pragmatism as well as the divergences emphasized between the two. I will argue that the teasing out of the similarities and the teasing out of the differences is important to a) a clearer understanding of both Wittgenstein and pragmatism; b) showing elements that make twentieth century philosophy unique; and c) shedding light on where philosophy is now, what issues and questions are being raised, and what possible solutions and answers are being offered.